I don't have a tradition for movies I watch but i do like The Gremlins. I don't honestly watch many Halloween themed movies (I'm not into horror), I guess Haunted Mansion counts as a Halloween movie.

I love watching The Nightmare Before Christmas! It never gets old!

The Nightmare Before Christmas. Classic.

Going with your theme of not scary Halloween movies, I'd have to recommend
House 2
The Burbs
Death Becomes Her

I like the first House film.

The first House film is awesome too. They made alot of good movies back then.

Army of Darkness is always a favorite, any time of year. I don't have any tradition when it comes to Halloween movies, but I do kinda stick to classic horror or comedy horror movies.
Event Horizon
Phantasm
House
Critters
Gremlins
Killer Klowns from Outer Space
All the classics, really. ..There are very few made in the last 10 years that I like, but the ones I know, everybody else does too. ...Splinter is an unexpected favorite.